Journal of Olly Headey. Co-founder & CTO at FreeAgent.

Boosting the signal

March 9th, 2021
I had a day "out of the office" yesterday (not to be confused with the previous 360 consecutive days out of the physical office since March 13, 2020). I just had a day off, which shouldn't be a particularly big deal. If anything urgent happened I would have received a phone call, otherwise I should easily be able to catch up with things on my return. I filter my email so it's a pleasant place these days, even after a few days without checking. Slack, on the other hand, is a complete disaster zone.

In my head I have long since departed all channels that I don't need to be in, and I only inhabit a few high-value, high signal-to-noise ratio ones. In reality, I have one day off and I'm snow-blinded by dozens of attention-seeking hashtags and red dots which results in a laborious routine of submissively channel-clicking and back-scrolling through history, desperately scanning for signs of value among a brain-frying array of links, mentions and updates. By the time I get to the end of it all I've forgotten most of it and bookmarked a few things which I will forget about and never return to until it's far too late. Even if I do remember, I will be unlikely to find those few nuggets of gold that I'm sure I came across because I can't quite make the search show me what I want. It's a context-switching nightmare. Is this progress? Is this effective collaboration and communication? Is this "work happening"? I recommend pressing Shift-Esc and moving on. If it's that important, someone will let you know.

The few channels I thought I was a member of turned out to be 157. At least I think so, because it's not something that Slack make particularly easy to find out. I guess highlighting this number to users might make them question the value Slack is adding to their day, and that question is probably not conducive to increasing weekly active users. I calculated it by browsing the channels then adding the Hide my channels filter if you wondered (972 channels – nearly 4 for every person!).

I've read a few books on the topic of Deep Work over the years which are interesting enough, but they can ultimately be summarised as something like: "turn off notifications and focus on one task for at least an hour or two". I even read recently about Deep Work as a Service. Concentration is now so hard to achieve it has been commoditised and outsourced to third parties to solve. This is dystopian stuff. 

Unless we act this will only get worse. Relentless group chat updates, back-to-back meetings leaving no time to work on the actual meeting actions, 15 people gathering in a room without a solid purpose. We've all been there. Leaders and managers in business have a real responsibility to do their own 'deep work' and concentrate on understanding the long-term costs of working this way. And that means the cost to employees as well as to the bottom line. 

Don't get me wrong, there is absolutely real value in these tools, it's just that it's suffocated by noise. To make progress, we all need to figure out how to suppress the noise in our workplaces and boost the signal.

How I implemented custom domain support with automatic TLS certs for my SaaS app

February 14th, 2021
Managing hosting and TLS certificates for customer-specified domains can be a challenge. In this article I explain how I solved this, with relative ease, for blogline.co.


When I first started working on Blogline (a fast, minimalist blogging platform), I had only planned to use it for my own blogs. Like most app developers (certainly those using Rails), I originally hosted it on Heroku, which has decent support for TLS if you're working with only a handful of known domains. Once I'd finished the early prototype, I decided it might be fun to turn it into a SaaS product that would allow customers to create a blog on their own domain in seconds. This didn't sound complicated technically – the main problem was how to manage TLS certificates.

📪 Free your Gmail Inbox

January 8th, 2021

Your inbox is probably a noisy place that you don't enjoy visiting. Am I right? I recently read the following tweet which motivated me to clear out my work inbox for 2021 (I only use Gmail for work).

You can do the same thing in Fastmail, Yahoo or whatever, but here’s how I did it in Gmail. If you’re using HEY this entire post is probably irrelevant! 

Music in 2020

December 28th, 2020
I thought about writing a “2020 in Review” article that was just a blank page, but rather than being facetious I thought I'd write about some of the music I listened to instead.

The problem with acronyms

December 10th, 2020
Reducing the use of unnecessary acronyms in your business will increase productivity and employee happiness, and reduce cynicism as you grow. Here's how.

Confusing vernacular isn’t a new thing to me, but I’ve noticed that an acronym[1] population steadily increases as projects, or entire companies, expand. I can sort of understand. When a company is bigger, there are more people and more things going on. More projects, more meetings, more presentations. Typing “Engaged User Growth Hack” becomes tedious the 14th time you write it in your proposal, so someone initialises it (EUGH) the first time and uses the acronym there on in. Once the document is circulated, it’s inevitable that at some point – it might take a few meetings, but eventually – it becomes common parlance. "How is the EUGH rate looking this week, Ted?"

One of the many problems you’re going to encounter in a growing business is a lack of clarity among staff. A successful business is one where employees understand things, and when they don’t it's okay because they know where to go to find the information required to understand things. 

Whether you’re a new hire reviewing an onboarding guide on your first day, or a seasoned employee reading the latest project proposal, you’re probably going to be faced with a sea of acronyms. The more there are, the more confused you'll be. This is bad for morale and bad for business, so it's your job as a leader in an organisation to spare everyone from this misery by eliminating acronyms as much as possible in your organisation. Here are my top tips.

👋 Farewell, CodeClan

October 29th, 2020
Around five and a half years ago I was asked by Polly if I would join a supervisory group who were tasked with understanding the feasibility of creating a digital skills academy for the software industry in Scotland. The idea was that this academy would train workers in software development over a 16 week course, then help them find jobs within the industry. The ultimate goal of this initiative was to help to bridge the increasing digital skills gap we were seeing in Scotland. Understandably, there were people who thought this couldn’t be done. Two of the biggest concerns were that the revenue model would never work and, perhaps more worryingly, that it wasn't possible to teach someone to code from scratch in 16 weeks. We went ahead and did it anyway.

After a lot of hard work (not on my part really!) the academy became a reality in June 2015 with the official announcement of CodeClan as "the UK’s first dedicated accredited software skills academy". The first cohort of students started in September 2015!

As with all startup businesses, the journey has been a rollercoaster of highs as well as lows. Some of the hard times were particularly pronounced since CodeClan is a social enterprise and the course was being offered at less than cost (the difference being made up by the partner programme). Yet, despite these challenges, the company has not only survived, it has thrived and forged ahead even in the face of the most difficult business challenge of modern times – a global pandemic.

CodeClan is now operating across three sites (Edinburgh, Glasgow, Highlands & Islands) and they recently celebrated 1,000 graduates which is an incredible milestone. At FreeAgent we have hired six CodeClan graduates over the years, all of who are amazing (and are all still with us).

It's a remarkable achievement.

Five years on, it's time for me to step down from the CodeClan board. I've thoroughly enjoyed being a board member, it has been a brilliant, rewarding journey – a privilege, really – and I've learned a huge amount from the experience, from my board colleagues as well as Polly (CodeClan Chair), Melinda (CEO) and her excellent team.

Thank you to everyone for letting me be part of it all and I look forward to seeing where CodeClan goes next!  👋

CodeClan board, circa 2019

Managing the books and boosting productivity

September 23rd, 2020
As FreeAgent nears the end of an epic migration to the cloud, there's an AWS-sponsored feature in a Times supplement about it today:

I saved a copy of the PDF for posterity.

Why you need to run all-hands meetings

August 19th, 2020
A typical all-hands meeting : photo @byfoul

We've been told that culture eats strategy for breakfast, and organisational health trumps everything else in business and I wouldn't disagree. Strong teamwork and effective communication are the best ways to build trust, and trust is at the heart of every successful team.

As a leader in a fast-growing company, one ceremony I've found crucial for encouraging effective communication is a weekly 'all-hands' meeting. This is an hour where everyone across the team congregates to share plans, ideas, stories. It's a place for sharing, to improve awareness, reinforce values and to help develop an inclusive culture which ultimately results in stronger trust. Every company should do this!

Using SWOT analysis to develop your engineering strategy

August 6th, 2020
Your first 90 days in a new leadership role (in particular, a VP Engineering or CTO role) will be largely spent in orientation. You'll be getting to know the ways and hows of the business in detail: its culture, its values, its structure, its current priorities, the things that work well and, of course, the things that don't. You need to see warts and all, leaving no stone unturned. 

A big investment of time will be getting to know your peers on the exec team (your first team): what makes them tick, what are their strengths, what skills are they working on ("weaknesses"), what are their frustrations, what are their interests. Similarly, you'll be getting to know the people you're managing as direct reports. First impression count. On both sides.

👋 HEY.com vs Fastmail. A review.

July 15th, 2020

I've been a fanboy of DHH and Jason of Basecamp since around 2006 when I first read Getting Real and started writing code in Rails. We used Basecamp (and for a brief time, Highrise) as our primary communication tool for the first few years of FreeAgent and it was a big influence from a product point of view. For the past 8 years though, I've not really used Basecamp products but I have remained a follower of the company and founders, reading their books and enjoying their Twitter rants. I'm still an ardent Rails fan as well 👨‍💻 

When I heard about HEY, I was immediately interested. Not because I've lost control of my inbox (I'm an order-freak and avid filterer so my inbox is generally a tranquil place), but because the HEY statement about why "Email’s a treasure" rang so true to me and because a brand-new, Rails-based, Basecamp product is always going to be pretty exciting to try.

I got my invite early and I've been kicking the tyres for a while, so I've written up a few thoughts to get them out there and to hear about what other people think.
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